PT93598B - Processo para a sintese da n-metil-3,4-dimetoxi-fenil-etilamina - Google Patents

Processo para a sintese da n-metil-3,4-dimetoxi-fenil-etilamina Download PDF

Info

Publication number: PT93598B
Authority: PT; Portugal
Prior art keywords: formula; approximately; temperature; hours; methyl
Prior art date: 1989-03-31

Application number

PT93598A

Other languages

English (en)

Portuguese (pt)

Other versions

PT93598A (pt

Inventor

Vincenzo Cannata

Giancarlo Tamerlani

Graziano Zagnoni

Original Assignee

Alfa Chem Ital

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-03-31

Filing date

1990-03-29

Publication date

1996-03-29

1990-03-29 Application filed by Alfa Chem Ital filed Critical Alfa Chem Ital

1990-11-20 Publication of PT93598A publication Critical patent/PT93598A/pt

1996-03-29 Publication of PT93598B publication Critical patent/PT93598B/pt

Links

238000000034 method Methods 0.000 title claims abstract description 16
230000015572 biosynthetic process Effects 0.000 title claims abstract description 9
238000003786 synthesis reaction Methods 0.000 title claims abstract description 9
WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 claims abstract description 14
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims abstract description 12
238000005904 alkaline hydrolysis reaction Methods 0.000 claims abstract description 4
RIVVYJWUHXMGSK-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)acetaldehyde Chemical compound COC1=CC=C(CC=O)C=C1OC RIVVYJWUHXMGSK-UHFFFAOYSA-N 0.000 claims abstract description 3
238000006114 decarboxylation reaction Methods 0.000 claims abstract description 3
150000001299 aldehydes Chemical class 0.000 claims abstract 2
239000007864 aqueous solution Substances 0.000 claims description 13
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 8
229910052700 potassium Inorganic materials 0.000 claims description 8
239000011591 potassium Substances 0.000 claims description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 7
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
VKFDPBQBFXWUIJ-UHFFFAOYSA-N n-ethyl-3,4-dimethoxy-n-methylaniline Chemical compound CCN(C)C1=CC=C(OC)C(OC)=C1 VKFDPBQBFXWUIJ-UHFFFAOYSA-N 0.000 claims description 7
229960005235 piperonyl butoxide Drugs 0.000 claims description 7
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
229910052708 sodium Inorganic materials 0.000 claims description 6
239000011734 sodium Substances 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
239000004593 Epoxy Substances 0.000 claims description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
239000012312 sodium hydride Substances 0.000 claims description 5
229910000104 sodium hydride Inorganic materials 0.000 claims description 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
239000002585 base Substances 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 3
159000000011 group IA salts Chemical class 0.000 claims description 3
229910000402 monopotassium phosphate Inorganic materials 0.000 claims description 3
235000019796 monopotassium phosphate Nutrition 0.000 claims description 3
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 claims description 3
LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 3
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
MCUHSYTVMNEJFT-UHFFFAOYSA-N butan-2-yl 2-chloroacetate Chemical compound CCC(C)OC(=O)CCl MCUHSYTVMNEJFT-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
AWDMDDKZURRKFG-UHFFFAOYSA-N potassium;propan-1-olate Chemical compound [K+].CCC[O-] AWDMDDKZURRKFG-UHFFFAOYSA-N 0.000 claims description 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
229910052796 boron Inorganic materials 0.000 claims 1
150000001768 cations Chemical class 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
230000000911 decarboxylating effect Effects 0.000 claims 1
VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 claims 1
QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 6
229910000033 sodium borohydride Inorganic materials 0.000 abstract description 5
239000012279 sodium borohydride Substances 0.000 abstract description 5
SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 abstract description 2
238000003476 Darzens condensation reaction Methods 0.000 abstract description 2
229940079593 drug Drugs 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract description 2
229960001722 verapamil Drugs 0.000 abstract description 2
150000001412 amines Chemical class 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
239000010410 layer Substances 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
239000000243 solution Substances 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 16
238000003756 stirring Methods 0.000 description 15
-1 alkyl radical Chemical class 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
239000012044 organic layer Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000012043 crude product Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
241000255890 Galleria Species 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
ASLSUMISAQDOOB-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1OC ASLSUMISAQDOOB-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229940080313 sodium starch Drugs 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
230000002522 swelling effect Effects 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/50—Ethers of hydroxy amines of undetermined structure, e.g. obtained by reactions of epoxides with hydroxy amines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Crystallography & Structural Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

PT93598A 1989-03-31 1990-03-29 Processo para a sintese da n-metil-3,4-dimetoxi-fenil-etilamina PT93598B (pt)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT8919959A IT1229214B (it)	1989-03-31	1989-03-31	Processo per la sintesi della n metil 3,4 dimetossifeniletilamina

Publications (2)

Publication Number	Publication Date
PT93598A PT93598A (pt)	1990-11-20
PT93598B true PT93598B (pt)	1996-03-29

Family

ID=11162654

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PT93598A PT93598B (pt)	1989-03-31	1990-03-29	Processo para a sintese da n-metil-3,4-dimetoxi-fenil-etilamina

Country Status (25)

Country	Link
US (1)	US5057624A (de)
EP (1)	EP0389876B1 (de)
JP (1)	JPH06102636B2 (de)
KR (1)	KR940011899B1 (de)
AR (1)	AR245930A1 (de)
AT (1)	ATE92467T1 (de)
AU (1)	AU627561B2 (de)
CA (1)	CA2013080C (de)
DD (1)	DD293109A5 (de)
DE (1)	DE69002500T2 (de)
DK (1)	DK0389876T3 (de)
ES (1)	ES2058644T3 (de)
FI (1)	FI102370B1 (de)
HR (1)	HRP940599B1 (de)
HU (1)	HU209947B (de)
IE (1)	IE63954B1 (de)
IL (1)	IL93762A (de)
IT (1)	IT1229214B (de)
NO (1)	NO170149C (de)
NZ (1)	NZ232975A (de)
PL (1)	PL162349B1 (de)
PT (1)	PT93598B (de)
SI (1)	SI9010634B (de)
YU (1)	YU48167B (de)
ZA (1)	ZA902003B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5840981A (en) *	1995-05-17	1998-11-24	Basf Aktiengesellschaft	Process for producing N-methyl-2(3,4 dimethoxyphenyl)-ethylamine
CN101580460B (zh) *	2009-05-26	2012-05-23	台州市知青化工有限公司	一种3，4-二羟基苯乙醇的合成方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3894051A (en) *	1973-07-05	1975-07-08	Colgate Palmolive Co	N-methylenedioxyphenylalkyl)-{62 -(alkyl)-disubstituted phenethylamines
US3997608A (en) *	1973-07-05	1976-12-14	Richardson-Merrell Inc.	N-substituted-dihydroxyphenethylamines
DE3338681A1 (de) *	1983-10-25	1985-05-09	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von n-methylhomoveratrylamin
GB8603765D0 (en) *	1986-02-15	1986-03-19	Beecham Wuelfung Gmbh & Co Kg	Compounds
IT1215409B (it) *	1987-04-08	1990-02-08	Alfa Chem Ital	Processo per la sintesi dell'alfa-(1-metiletil)-3,4-dimetossibenzeneacetonitrile.

1989
- 1989-03-31 IT IT8919959A patent/IT1229214B/it active
1990
- 1990-03-15 ES ES90104931T patent/ES2058644T3/es not_active Expired - Lifetime
- 1990-03-15 DE DE90104931T patent/DE69002500T2/de not_active Expired - Fee Related
- 1990-03-15 EP EP90104931A patent/EP0389876B1/de not_active Expired - Lifetime
- 1990-03-15 DK DK90104931.2T patent/DK0389876T3/da active
- 1990-03-15 AT AT90104931T patent/ATE92467T1/de not_active IP Right Cessation
- 1990-03-15 KR KR1019900003444A patent/KR940011899B1/ko not_active Expired - Fee Related
- 1990-03-15 ZA ZA902003A patent/ZA902003B/xx unknown
- 1990-03-16 IL IL9376290A patent/IL93762A/en unknown
- 1990-03-19 NZ NZ232975A patent/NZ232975A/xx unknown
- 1990-03-26 CA CA002013080A patent/CA2013080C/en not_active Expired - Fee Related
- 1990-03-27 DD DD90339109A patent/DD293109A5/de unknown
- 1990-03-27 AR AR90316461A patent/AR245930A1/es active
- 1990-03-28 PL PL28450790A patent/PL162349B1/pl unknown
- 1990-03-29 SI SI9010634A patent/SI9010634B/sl unknown
- 1990-03-29 JP JP2082896A patent/JPH06102636B2/ja not_active Expired - Fee Related
- 1990-03-29 PT PT93598A patent/PT93598B/pt not_active IP Right Cessation
- 1990-03-29 YU YU63490A patent/YU48167B/sh unknown
- 1990-03-30 FI FI901611A patent/FI102370B1/fi not_active IP Right Cessation
- 1990-03-30 NO NO901454A patent/NO170149C/no not_active IP Right Cessation
- 1990-03-30 HU HU902025A patent/HU209947B/hu not_active IP Right Cessation
- 1990-03-30 AU AU52470/90A patent/AU627561B2/en not_active Ceased
- 1990-03-30 IE IE117190A patent/IE63954B1/en not_active IP Right Cessation
- 1990-03-30 US US07/502,038 patent/US5057624A/en not_active Expired - Lifetime
1994
- 1994-09-26 HR HRP-634/90A patent/HRP940599B1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
HRP940599A2 (en)	1997-06-30
IT1229214B (it)	1991-07-25
DD293109A5 (de)	1991-08-22
NO170149B (no)	1992-06-09
SI9010634A (en)	1997-08-31
NZ232975A (en)	1991-11-26
AR245930A1 (es)	1994-03-30
HUT53865A (en)	1990-12-28
JPH02289539A (ja)	1990-11-29
US5057624A (en)	1991-10-15
IE63954B1 (en)	1995-06-28
YU48167B (sh)	1997-07-31
JPH06102636B2 (ja)	1994-12-14
DK0389876T3 (da)	1993-09-27
ES2058644T3 (es)	1994-11-01
SI9010634B (sl)	1998-06-30
IT8919959A0 (it)	1989-03-31
HU902025D0 (en)	1990-07-28
HU209947B (en)	1994-12-28
HRP940599B1 (en)	1998-04-30
PL162349B1 (pl)	1993-10-30
ATE92467T1 (de)	1993-08-15
KR900014310A (ko)	1990-10-23
KR940011899B1 (ko)	1994-12-27
IL93762A (en)	1994-07-31
AU627561B2 (en)	1992-08-27
NO170149C (no)	1992-09-16
EP0389876A1 (de)	1990-10-03
CA2013080A1 (en)	1990-09-30
IE901171L (en)	1990-09-30
FI901611A0 (fi)	1990-03-30
FI102370B (fi)	1998-11-30
ZA902003B (en)	1990-12-28
FI102370B1 (fi)	1998-11-30
EP0389876B1 (de)	1993-08-04
DE69002500D1 (de)	1993-09-09
IL93762A0 (en)	1990-12-23
NO901454D0 (no)	1990-03-30
PT93598A (pt)	1990-11-20
DE69002500T2 (de)	1994-01-13
NO901454L (no)	1990-10-01
CA2013080C (en)	1997-07-22
YU63490A (en)	1991-10-31
AU5247090A (en)	1990-10-04

Legal Events

Date	Code	Title	Description
1996-03-29	FG3A	Patent granted, date of granting	Effective date: 19951221
2005-08-31	MM3A	Annulment or lapse	Effective date: 20050621

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